Crossroads: Ownership Conversations with Chris Chasteen of Content Cucumber and Silicone Depot

Scratch Entrepreneur

Today’s show is the fourth in our series of on-air coaching sessions between veteran executive coach David Quick and an entrepreneur who sits at a crossroads. A big decision point in his or her business.

Our guest today has built a painless way for your business to share your expertise with the world. His team includes rock star writers, street-wise marketing gurus, and analytics obsessed techies. When you put that all together, Content Cucumber has created a one stop shop for building your brand and sharing your perspective with the world. Our guest today is co-founder Chris Chasteen who started as a financial investor in the project but then felt so connected with it he up his connection to a full-fledged member of the founding team.

Topics discussed include:

• Podcasts we’re listening to (4:30)
• Chris’ Crossroad (7:30)
• With money out of the equation, which business would Chris choose? (11:30)
• The steps to making Content Cucumber profitable (17:30)
• Dave’s tip #1: Setting milestones and the steps to achieve them (26:00)
• Dave’s tip #2: Prepping for the ownership conversation (32:00)
• Dave’s tip #3: Create a laundry list of loose ends, if the conversation goes well (35:30)

Mentioned in the episode:

• BeeCorp
• Enrollment Fuel
• Shine Insurance
• How I built This
• Scratch Entrepreneur
• BTown LowDown
• Up & Vanished

Special thanks to Chris Chasteen for taking the time to share his crossroads with us

Contributors to this episode include:

• Host - Jeremy Goodrich
• Co-host - David Quick
• Music - Mark Vinten
• Editing - Christopher Lang

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